AI Chatbot Showdown A Surprising Weeks Winner

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I’ve written extensively about AI assistants. I’ve compared their features, detailed the latest updates, and tested various prompts to find the most effective ones.

However, to truly determine which AI assistant best suits me and my productivity needs, I needed to use each one exclusively, without the option of switching to another.

If you've followed my work, you know my fondness for “prompt dusting” — using one chatbot's output as input for another to refine results. But for this specific test, that technique was off-limits.

For one week, I conducted a full-scale experiment. I rotated through ChatGPT (GPT-4o), Claude 4 Sonnet, Gemini 2.5 Pro, Perplexity, and DeepSeek as my daily assistant.

The only rule was strict: I had to use each one exclusively for a full 24 hours, with no switching mid-day. To ensure compliance, I reluctantly logged out of all other chatbots I wasn't currently testing.

I put these assistants through their paces, tackling tasks from researching why my dishwasher kept tripping and finding tips to avoid toddler tantrums, to planning meals and assisting with my workflow. It was a test of how well they could keep up with my chaotic life.

By the end of the week, only one of them truly felt like it could become a permanent fixture.

Day 1: ChatGPT-4o

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ChatGPT offers Voice and Vision capabilities, which I frequently use for hands-free assistance. When my son’s soccer tournament location changed suddenly while I was driving, I used the assistant to quickly figure out where I needed to be in ten minutes. The chatbot responded effectively and even advised me to stay calm as I pulled over to search for new directions.

Another way I utilized ChatGPT on its designated day was by summarizing text messages from a group chat of 15 very active moms. Needing to catch up quickly, I uploaded a few screenshots into the app, and ChatGPT helped me grasp the gist of the conversation seamlessly.

The human-like element of ChatGPT, especially during life’s hectic moments, is where this chatbot truly excels. I found it faster and more proficient at voice, image, and memory tasks. It remembered my preferences for meal planning and even helped me brainstorm surprisingly creative ideas for my father-in-law’s birthday.

Where it shined:

• Memory and custom instructions made it feel personal
• Great for brainstorming and creativity
• Solid image interpretation
• Ideal emotional support

Where it lagged:

• Sometimes still too eager to please, less critical than I wanted
• Multimodal features work best in the app, not the browser

Day 2: Claude 4 Sonnet

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Transitioning from ChatGPT to Claude was a bit challenging. Although it has a new voice feature, it’s not as refined, so I mostly stuck to text-based interactions.

Claude is also thoughtful, sometimes excessively so. The chatbot provided deeply reasoned answers and beautifully written prose, but it could become a bit verbose.

Unlike ChatGPT, where I feel like I’m chatting with a friend, interacting with Claude can sometimes feel like talking to a philosophy major. The chatbot feels far less personal and struggles with handling numerous sporadic questions.

For instance, when I was meeting a friend for dinner at an unfamiliar restaurant, Claude had difficulty providing directions. When I mentioned it was next to a park, the assistant suggested I call the park ranger, which wasn't ideal.

The assistant was helpful when I received an extremely long email from my literary agent that I needed to respond to quickly but didn’t have time to read thoroughly. It helped craft a suitable email based on a summary of the original message.

An unexpected win for Claude was its ability to handle emotional nuance. When I was struggling to word a delicate personal message that carried some emotional weight, Claude delivered impressively.

Claude's responses weren’t just grammatically clean; they were empathetic, balanced, and thoughtful. If you ever need to write a message that’s both clear and kind, Claude is surprisingly good at finding that tone.

Where it shined:

• Incredible at nuanced reasoning and long-term structure
• Calm, articulate tone
• Great with analysis and summarization

Where it lagged:

• Less helpful for immediate questions like directions
• Voice feature not great

Day 3: Gemini Live

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Gemini is a tool I use regularly, and I definitely missed it during my ChatGPT and Claude days. The chatbot is fast, visually aware, and connected to Google’s ecosystem — which helps keep me organized throughout the week.

From searching for real-time information or pulling from Gmail and Docs, this is usually my go-to bot. However, when it comes to creativity, Gemini can be somewhat lackluster.

Gemini Live was helpful when I realized the chicken I bought for dinner was two days past its expiration date. Was it still safe to eat? It advised against it and then made suggestions based on what it could see in my fridge and pantry. I ended up making crispy chicken wraps for the family that were a big hit.

Another instance where Gemini helped was at bedtime when my kids were being particularly difficult. Parents of young children know how challenging bedtime can be. You're exhausted, and the kids are looking for any excuse to stay up.

I turned on Gemini Live and asked for help. With a simple prompt of “Help me get my kids to bed!” it came up with some genuinely helpful tips, including whispering (even though I wanted to scream) to help calm the kids who were practically bouncing off the walls.

Where it shined:

• Fantastic for Google Workspace integration
• Excellent at organizing info and finding sources
• Strong math and chart-making skills

Where it lagged:

• Creativity was underwhelming
• Occasionally hallucinated formatting or skipped nuance

Day 4: Perplexity AI

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Perplexity is like a super-charged research intern. It provides real citations, quick summaries, and real-time web results. However, it’s not really a conversational partner — more like a search engine dressed as a chatbot.

On the day I used Perplexity, I was drafting a story and needed to double-check the launch date of a specific AI model. Perplexity pulled up the date instantly, along with three verifiable sources. No hallucinations.

Actually, I’ve never seen Perplexity hallucinate. Have you? Let me know in the comments. I’m genuinely curious about this.

That same day, with summer hitting New Jersey, I was looking for a small but powerful fan for my office and wanted to compare prices. Perplexity laid out side-by-side specifications and recent reviews from trusted sites — all in under 30 seconds. It felt like skipping three Google tabs.

I also used Perplexity to catch up on news and newsletters I’d saved for my Perplexity day. (Was that cheating?) It pulled from current articles, summarized key updates, and provided links for further exploration. Less noise, more clarity.

Where it shined:

• Best for fast, factual, source-backed answers
• Great for staying up-to-date with news or product research
• Fast and efficient

Where it lagged:

• Lacks tone, personality, or memory
• Not ideal for brainstorming or big creative projects

Day 5: DeepSeek

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DeepSeek was the dark horse of the week. I usually use this one for creative tasks, so I was genuinely impressed with how it performed as an AI assistant. While not as well-known or widely used, it’s quickly proving it can compete with big names like ChatGPT and Gemini.

DeepSeek is incredibly capable when it comes to reasoning, coding, and vision-based tasks.

In fact, my first test was visual. I uploaded a photo of my daughter’s field trip supply list (crumpled and slightly coffee-stained) and asked DeepSeek to organize it into a shopping checklist by store. Not only did it read the handwriting correctly, but it also suggested which items I could get from Amazon, Target, or Walmart. It even gave me estimated prices.

Later, I asked DeepSeek to help explain why my cat was coughing and sneezing excessively. It provided a detailed yet understandable breakdown of possible causes and even helped me find vets in the area (although we already have one, it demonstrated its capability as an assistant).

I noticed that it wasn't as chatty as ChatGPT, but it was definitely “friendly.” DeepSeek shines when you need serious problem-solving or tech-heavy tasks done quickly.

Where it shined:

• Exceptional vision analysis and image-based reasoning
• Strong logical thinking and technical explanations
• Great for coding, math, and structured planning

Where it lagged:

• Limited personality or warmth in conversation
• Not ideal for emotional tone or open-ended brainstorming

Final Verdict: The One I’d Keep

With the unpredictability of each day, the “you get what you get” nature of the test turned into quite an adventure. But, after a week of controlled AI assistance, ChatGPT came out on top, with Gemini Live as a very close second.

ChatGPT isn’t perfect, but its memory aspect is a huge asset for me. It knows me best, so I don’t have to repeat myself. With memory enabled and custom instructions dialed in, it was the only one that felt like it was adapting to me — not the other way around.

This chatbot strikes the best balance between creativity, utility, and usability. It also just feels the most like a true assistant. It knew my tone, anticipated my needs, and helped me work and think better.

That said, I have found that using them all in a hybrid way is the most effective approach. I’ll always keep Claude around for deep dives and Perplexity for quick research. Gemini is intertwined in my workflow, so there’s no way that one is going anywhere.

Bottom line: I’m glad I don’t have to make a choice.

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